10 things I learned from Paul Singh

Paul Singh’s North American tech tour stopped in Waterloo. There were a lot of great events to learn from Paul, but the best advice is the kind he shares over a beer or a run.

Paul framed most of his talks as investor advice, but most of it applies equally to Sales and Marketing.

1. Know the economics of your customer

Prospect investors like you would your customers. Learn what metrics your investors need to hit and how the economics of their fund works. They need to believe you’ll return 4x their fund.

If you spend more than 50% of your time talking about product, you have a problem with explaining your product or market fit. With investors, incorporate your company stage into your story: get to revenue and pipeline quickly to frame the conversation.

2. Business etiquette ≠ dinner party etiquette

People in a business relationship expect business behaviour: make the ask. There’s a time for polite chit-chat, and a time for selling. If you’re in a business context or a meeting, don’t leave your ask for the last minute.

3. Complaining about your local community is lazy

Paul used to be a brick layer. His market was limited to people who wanted a stone patio in a 100 mile radius of his home — the distance he could practically drive to work.

SaaS companies don’t have geographic restrictions. It’s never been easier to raise money or sell your product in a location you don’t live in. Entire transactions happen virtually, and you can fly anywhere in a couple of hours.

If your local angel community is tapped out, or you can’t find customers in your local community, find somewhere you can. It doesn’t mean you need to relocate your business, but you need to expand your geographic market.

4. Be the prophet from afar

Everyone goes to the Valley, which means the Valley is crowded and noisy.

Odds are there are investors or prospects in another city, like Oklahoma, that you can connect with much easier. Companies coming from Waterloo are perceived a lot larger than we think. Go to these cities, leverage being the prophet from afar, and have the local tech communities create meetings and speaking opportunities for you.

5. Get better are doing more

When you go to the gym for the first time, lifting weights is terrible. You can barely lift 10 pounds, yet someone a few feet over has a bar stacked with weights. They didn’t get there overnight. When lifting 10 pounds got easy, they lifted more.

As we look at companies a stage or two ahead of ourselves, we learn that over time we get better at doing more.

6. Go running

I took Paul for an early morning run to show him around Kitchener-Waterloo. It was a great way to learn about him outside of the startup hub context.

Paul talks about the 4-minute mile: we always thought it was impossible for a human to run a 4-minute mile, until someone did. Then a whole bunch of people did it in short proximity. Once we prove something is possible in our companies or communities — getting sales, getting funding — it becomes easier to do it again, and again, and again.

7. Love your stories

Paul has his script down: he has a set of stories that tell founders the type of investor he is. These stories drip in his background, his success, his learnings, and his interests. What amazed me was the consistency of Paul’s storytelling and how he is able to tell the same stories with energy and excitement every day.

Do this for your pitch. Do this for your sales process.

8. Be a media company

“Anyone can fly to Waterloo. I’m the only one in an Airstream.”

Paul is driving around the country in an Airstream because nobody else is. He’s on Snapchat. He’s on Twitter. He sends out a newsletter of interest articles. He’s doing this so his customers (founders, syndicate partners) get to know him. It’s a controlled brand message through his own media outlet.

Money is a commodity. For Paul to be involved in the best early-stage deals around the country, his brand makes him appeal to a certain kind of founder. He has built-in differentiation and stands out in a crowded market.

This is an important lesson for every company.

9. Notability v.s. Credibility

Credibility is why I should trust you. This is your background and experience. You need it, but as you’re building your business you also need to be notable. People need to know who you are, hear what you think, and see you as the expert in your field.

Credibility gets you started, but notability is how you scale your business

10. Don’t Tweet this

The best stories are the ones that don’t get shared online. Build a community of like-minded founders. Restrict the group to those who have at least one dollar in revenue from someone they don’t know. Share the important stories, especially the hard ones.

But don’t Tweet them.


Paul Singh is a great DJ. He says he likes country, but early 90s hip hop seems to be where his heart truly lives.